Abstract
Abstract The carbonylation of 1, 5, 9-cyclododecatriene has been carried out in ethanol in the presence of palladium chloride; mono- and diesters have thus been obtained without ring contraction. It has been observed, by means of a study of the NMR and infrared spectra, that the first attack of carbon monoxide occurred at the trans double bond, giving ethyl cyclododecadienecarboxylate. The second attack of carbon monoxide occurred randomly, giving an isomeric mixture of ethyl cyclododecenedicarboxylate. No triester was obtained even under prolonged carbonylation. The true catalyst has been found to be metallic palladium, and the presence of hydrogen chloride has been found to be essential for the catalysis. The oxidation of ethyl cyclododecadienecarboxylate, followed by esterification, has given ethyl succinate and 1, 3, 6-hexanetricarboxylate. This result indicates that the double bonds of ethyl cyclododecadienecarboxylate remain at the original positions.
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